The 19-year-old will chase a second AFL flag in as many seasons when the Brisbane Lions face Fremantle in Saturday's decider.
Brother Will is pursuing a third-straight title and, fresh off a starring role in Saturday's classic preliminary defeat of Hawthorn, can become the first player to win three consecutive Norm Smith Medals if he lights up the MCG again.
Their father Marcus was central to the Lions' three-peat between 2001-03 and Levi admits it would be the "icing on the cake" to help this Lions side replicate that feat.
But Levi's trophy cabinet is already bursting, given he won three-straight Talent League titles with Sandringham before he was drafted.
There were two Associated Public Schools premierships with Brighton too, including as co-captain in 2024.
"You can never get bored of winning," Ashcroft smiled on Monday after recounting a Hawthorn victory he described as "the most insane game he's played, by a mile".
"I just love winning. It's what everyone wants to do, and especially with these guys. It's a special place.
"And I've thought about that, that some guys play 15, 20 years and don't win one or even involved in one. So I'm extremely grateful."
Ashcroft is preparing to play an even greater role if midfield star Lachie Neale's one-match ban for striking Hawthorn's Jack Ginnivan is upheld.
"It'll be disappointing if he doesn't play; he's a huge part of the team and in some great form," he said.
"I'm banking on him being there.
"But we have a good midfield that surrounds him and if it goes that way we're ready to go."
The father-son pick and his older brother have slotted straight into a stacked Lions squad, having grown up shadowing their father when he was the football manager of the fledgling Gold Coast AFL club.
"It's the narrative, that we were born to play in these moments," Ashcroft said.
"But it's all the hard work we've done behind the scenes, to feel ready and prepared for these moments, to really attack them and make an impact.
"Will ... elevates himself when those big moments come."
The Ashcrofts are among many young Lions blessed with immediate success.
Ty Gallop is preparing for his second grand final in just his 27th AFL game; 70-gamer Logan Morris could win his third title on Saturday, while 17 of Darcy Wilmot's 107 AFL games have been finals.
"It can be about timing and luck, when your career comes and goes," veteran Lions defender Darcy Gardiner, in his 13th season at the club, said.
"So they've come at a good time, but they're playing a huge part in us winning, not just getting by. They're key players."
Levi loved watching footage of his father's games as a kid, but said there had never been great discussions about his achievements.
"He just encouraged us to play and enjoy it and now it's come to this moment and the chance to win three and join him in history," he said.
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